Selenium Dioxide → 5-Cyano-6-formyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]([NH:10][CH:11]([CH3:14])[CH2:12][CH3:13])=[N:7][C:8]=1[CH3:9])#[N:2].[Se](=O)=[O:21]>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:6]([NH:10][CH:11]([CH3:14])[CH2:12][CH3:13])=[N:7][C:8]=1[CH:9]=[O:21])#[N:2]Participants
4
Procedure
26.1 g of 5-cyano-6-methyl-2-[(1-methylpropyl)amino]-3-pyridine-carboxylic acid, ethyl ester (0.1 mol) and 13 g of selenium dioxide are refluxed together in dioxane for 24 hours. After this time the selenium is filtered off and the solvent removed in vacuo. The resulting oily residue is crystallized with ether. Yield 19 g (69%); m.p. 37°-38° C. (methanol).